CN102399125B - Method for separating mixture of m-ethyltoluene and p-ethyltoluene from C9 aromatics - Google Patents
Method for separating mixture of m-ethyltoluene and p-ethyltoluene from C9 aromatics Download PDFInfo
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Abstract
The invention discloses a method for separating a mixture of m-ethyltoluene and p-ethyltoluene from C9 aromatics. The method comprises the following steps of: (1) mixing a C9 aromatics mixture and an accelerator, and sending into a heavy component eliminating tower, introducing a light component from the top of the tower, introducing a heavy component from a tower kettle; wherein the weight ratio of the C9 aromatics mixture to the accelerator is 1:0.05-0.5; (2) sending the light component from the step (1) into a light component eliminating tower, introducing the mixture of m-ethyltoluene and p-ethyltoluene from the tower kettle; (3) sending material flow introduced from the light component eliminating tower in the step (2) to an accelerator removal tower, introducing the accelerator from the tower top, introducing the material flow containing normal propylbenzene and isopropylbenzene from the tower kettle. The accelerator is acetonitrile and propionitrile. The mixture of m-ethyltoluene and p-ethyltoluene obtained by the method of the invention has the advantages of high purity, high yield and obvious separation effect.
Description
Technical field
The present invention relates to organic chemistry filed, say further, relate to a kind of from C9 aromatic the method for compartment, p-methyl-ethylbenzene mixture.
Background technology
The exploitation of C9 aromatic deep processing technology and the utilization of various components are the problems that people are concerned about always.The composition of different chemical-process by-product C9 aromatic cuts is different, and its basal component such as sym-trimethylbenzene, unsym-trimethyl benzene, the first and second benzene etc. are all important chemical resources.The first and second benzene comprise the neighbour,, to three kinds of isomer, proportion is higher in the C9 aromatic mixture, especially can account for 25%-30% in reformation C9 aromatic cut.Because boiling-point difference between m-methyl ethylbenzene and p-methyl-ethylbenzene is only 0.7 ℃, be difficult to disposablely to separate fully, so C9 aromatic be isolated mostly be between, the p-methyl-ethylbenzene mixture.
CN1958538A discloses a kind of method of separating C9 aromatic, comprise the C9 aromatic mixture is carried out prefractionation, intercepting contains the enriched fraction of sym-trimethylbenzene and o-methylethylbenzene, and by-product contains n-proplbenzene, isopropyl benzene simultaneously,, low boiling mixture product and the unsym-trimethyl benzene product of p-methyl-ethylbenzene; The enriched fraction that will contain sym-trimethylbenzene and o-methylethylbenzene is introduced the double solvent extraction rectifying tower, under solvent pairs synergistic extraction effect, obtains sym-trimethylbenzene product and o-methylethylbenzene product.Wherein said prefractionation step can adopt precise distillation or extracting rectifying, and when adopting precise distillation technique, stage number could effectively be separated sym-trimethylbenzene greater than 200, obtain just the containing of higher yields, isopropyl benzene between, the mixture of p-methyl-ethylbenzene.How this technology does not relate to and further just separating, isopropyl benzene, obtain high purity (greater than 95%) more between, the p-methyl-ethylbenzene mixture.
(print during chemical industry in the literature, the 2nd phase of calendar year 2001, P.25) in the author to adopt number of theoretical plate be the experiment that 60 glass filler tower has carried out precision fractional distillation compartment, p-methyl-ethylbenzene mixture, be to carry out precise distillation under the condition of 20-40 in reflux ratio, can obtain purity greater than between 95%, p-methyl-ethylbenzene and o-methylethylbenzene, but the author do not provide from, the p-methyl-ethylbenzene mixture just removing, the experimental data of isopropyl benzene and, the yield of p-methyl-ethylbenzene mixture.
Chinese patent 200810225604.0 discloses a kind of method of separating C9 aromatic.The method two tower separation process, weight-removing column pressurized operation, lightness-removing column decompression operation.The method of this invention only improves the weight-removing column working pressure on the existing technique of change basis hardly, reduce the lightness-removing column working pressure, but energy efficient not only, and obtain between, the purity of p-methyl-ethylbenzene mixture compares slightly with existing technique with yield and is improved.Owing to adopting the precise distillation method, separate required rectifying tower plates number still more (〉=120), reflux ratio high (〉=35), energy consumption is still quite high, and yield is lower, and quality product is relatively poor.
Due to, the p-methyl-ethylbenzene mixture serves many purposes, as between its dehydrogenation product, p-methylstyrene mixture purposes is very extensive, can carry out copolymerization, composite adhesives, resin, printing ink, dry cleaning composition, coating etc. from multiple the 3rd different monomer respectively; Under catalyst action, it is oxidable is tolyl acid, and hydrogenation generates the ethyl cyclohexylenedinitrilotetraacetic acid, is applied in siccative, wood preservative, synthetic detergent and the agrochemical aspect of paint.Can therefore, rationally make good use of this part resource of the first and second benzene, be especially a reform key of C9 aromatic comprehensive utilization of C9 aromatic.
In order to solve the existing problem that exists in compartment, p-methyl-ethylbenzene mixture technology from the C9 aromatic raw material, provide a kind of economy, separate obtain between high purity and high yield, the method for p-methyl-ethylbenzene product is very necessary.
Summary of the invention
Be to solve problems of the prior art, the invention provides a kind of from C9 aromatic the method for compartment, p-methyl-ethylbenzene mixture.Have advantages of compartment, p-methyl-ethylbenzene mixture purity is high and yield good.
The purpose of this invention is to provide a kind of from C9 aromatic the method for compartment, p-methyl-ethylbenzene mixture.
when adopting the rectification method separating mixture, in rectifying tower, the liquid-vaqor interface of system is very large, vapour in rectifying, the mass transfer of liquid two-phase carries out in liquid-vaqor interface, the quality of the effect of separation mixture, the vapour phase that not only depends on system, the thermodynamic property of liquid phase and the rule of stream-liquid phase balance, but also depend on that the surface properties of liquid and various component break away from the difference of the speed speed of vapour phase from fluid surface, therefore, can use to increase the relative volatility that wish is separated the purpose component, the special extract rectification method that can make again the purpose component break away from sooner roll body surface and transfer to vapour phase realizes the separation of the system that boiling point is close very much.In order to achieve the above object, add a kind of special solvent in rectifying tower, not only increase the adding of this special solvent wish and separated the relative volatility of purpose component, and the purpose component is shifted quickly to vapour phase from liquid phase than other component, above-mentioned special extract rectification method is named as benzene with catalytic rectifying method, and special solvent used claims to urge agent.
In general, urge the selection of agent mainly to consider from the following aspects:
(1) urge agent to separate the purpose component with wish larger seemingly avidity and larger surfactivity are arranged;
(2) urge agent not with raw material in any component generation chemical reaction, do not form azeotrope yet;
(3) urge the agent boiling point low than each component boiling point in raw material, can recycle by conventional distillation;
(4) urge agent and separated component intermiscibility better, avoid occuring demixing phenomenon;
(5) urge agent to want nontoxic or hypotoxicity, non-corrosiveness, Heat stability is good and cheap, easily obtain.
What the present invention adopted is exactly above-described benzene with catalytic rectifying method, adds the urgency agent in rectifying, and described urgency agent is a kind of in acetonitrile and propionitrile, preferred propionitrile.
Described method comprises following steps:
(1) C9 aromatic mixture and urgency agent are sent into weight-removing column after mixing, drawn the light constituent that comprises n-proplbenzene, isopropyl benzene, m-methyl ethylbenzene, p-methyl-ethylbenzene and urgency agent by the weight-removing column tower top, drawn the heavy constituent that contains sym-trimethylbenzene, o-methylethylbenzene, unsym-trimethyl benzene and hemimellitene by the weight-removing column tower reactor;
The weight ratio of described C9 aromatic mixture and urgency agent is: 1: 0.05～0.5, preferred: 1: 0.05～0.3, more preferably: 1: 0.05～0.1;
(2) light constituent described in step (1) is sent into lightness-removing column, drawn the logistics that includes n-proplbenzene, isopropyl benzene and urgency agent by the lightness-removing column tower top, draw m-methyl ethylbenzene, p-methyl-ethylbenzene mix product by the lightness-removing column tower reactor;
The logistics of (3) lightness-removing column tower top described in step (2) being drawn is sent into to take off and is urged the agent tower, urges the agent tower top to draw the urgency agent by taking off, and urges agent tower tower reactor to draw the logistics that includes n-proplbenzene, isopropyl benzene by taking off.
The equipment of using in the method for the invention is the equipment that usually adopts in C9 aromatic rectifying as lightness-removing column, weight-removing column.
In concrete operations, can implement by following condition:
Described weight-removing column stage number is 30～90, the weight-removing column tower top temperature is 80～180 ℃, the weight-removing column tower top pressure is 0.1～0.5MPa, weight-removing column tower reactor temperature is 170～210 ℃, weight-removing column tower reactor pressure is 0.12～0.8MPa, reflux ratio is 2～20, preferably: the weight-removing column stage number is 40～60, the weight-removing column tower top temperature is 90～160 ℃, the weight-removing column tower top pressure is 0.1～0.3MPa, weight-removing column tower reactor temperature is 175～190 ℃, and weight-removing column tower reactor pressure is 0.12～0.4MPa, and reflux ratio is 7～12;
Described lightness-removing column stage number is 30～200, the lightness-removing column tower top temperature is 80～170 ℃, the lightness-removing column tower top pressure is 0.1～0.5MPa, lightness-removing column tower reactor temperature is 170～210 ℃, lightness-removing column tower reactor pressure is 0.12～0.8MPa, reflux ratio is 5～20, preferably: the lightness-removing column stage number is 50～70, the lightness-removing column tower top temperature is 90～160 ℃, the lightness-removing column tower top pressure is 0.1～0.3MPa, lightness-removing column tower reactor temperature is 175～190 ℃, and lightness-removing column tower reactor pressure is 0.12～0.4MPa, and reflux ratio is 7～14;
Describedly take off that to urge agent tower stage number be 5～20, taking off urgency agent column overhead temperature is 80～140 ℃, and taking off urgency agent column overhead pressure is 0.1～0.5MPa, and taking off urgency agent tower tower reactor temperature is 150～190 ℃, taking off urgency agent tower tower reactor pressure is 0.11～0.8MPa, and reflux ratio is 2～15; Preferably: taking off urgency agent tower stage number is 8～15, taking off urgency agent column overhead temperature is 80～120 ℃, and taking off urgency agent column overhead pressure is 0.1～0.3MPa, and taking off urgency agent tower tower reactor temperature is 155～175 ℃, taking off urgency agent tower tower reactor pressure is 0.11～0.4MPa, and reflux ratio is 2～5.
C9 aromatic mixture of the present invention can be from oil, xylene isomerization by-product at the bottom of the platinum reforming tower, preferably in the middle of it, the content of p-methyl-ethylbenzene is 15～40 % by weight.The C9 aromatic of different sources forms slightly different, and those skilled in the art can be according to practical situation adjustment operation processing condition.
Method of the present invention has the following advantages:
1, adopt of the present invention from C9 aromatic the stage number of the required rectifying tower of compartment, p-methyl-ethylbenzene mixture method the chances are stage number 1/2 that rectification method separates required tower, from the data on reflux ratio one hurdle more as can be known, the present invention per hour treatment capacity of C9 aromatic is about 2.5 times of left and right of rectification method, can reach the purpose of less investment, high yield.
2, between adopting that the method for the invention obtains, p-methyl-ethylbenzene mixture purity and yield be significantly improved, and can reach high-quality, the purpose of high yield.
Description of drawings
Fig. 1 of the present invention from C9 aromatic the schematic flow sheet of compartment, p-methyl-ethylbenzene mixture.
Description of reference numerals:
Equipment class: A1 mixing tank, B1 weight-removing column, B2 lightness-removing column, C1 take off urges agent tower, D1 the first condenser, D2 the second condenser, D3 the 3rd condenser, E1 the first return tank, E2 the second return tank, E3 the 3rd return tank, F1 the first reboiler, F2 the second reboiler, F3 the 3rd reboiler
Logistics class: 1 C9 aromatic raw material, 2 replenish fresh urgency agent, agent is urged in 3 circulations, 4 contain urgency agent and C9 aromatic raw material, and 5 contain n-proplbenzene, isopropyl benzene, m-methyl ethylbenzene, p-methyl-ethylbenzene and urgency agent component, 6, contain sym-trimethylbenzene, o-methylethylbenzene, unsym-trimethyl benzene and hemimellitene component, 7 contain n-proplbenzene, isopropyl benzene and urgency agent, 8 m-methyl ethylbenzenes, p-methyl-ethylbenzene mix product, and 9 contain n-proplbenzene, isopropyl benzene component
Embodiment
Below in conjunction with embodiment, further illustrate the present invention.
as shown in Figure 1, in mixing tank A1, enter the middle and lower part of weight-removing column B1 after urging agent and C9 aromatic raw material 1 to mix, weight-removing column B1 tower top distillates steam 5, 5 comprise n-proplbenzene, isopropyl benzene, m-methyl ethylbenzene, the logistics of p-methyl-ethylbenzene and urgency agent, enter tower top the first return tank E1 after the first water cooler D1 is cooling, a part is through flowing into the tower top of weight-removing column B1 as refluxing, a part enters the middle and lower part of lightness-removing column B2, lightness-removing column B2 tower top distillates steam 7, 7 comprise a n-proplbenzene, the logistics of isopropyl benzene and urgency agent, enter tower top the second return tank E2 after the second water cooler D2 is cooling, a part flows into the tower top of lightness-removing column B2 as refluxing, a part enters takes off the middle part of urging agent tower C1, urge agent tower C1 tower top to distillate steam 3 taking off, 3 is the urgency agent that recycles, enter tower top the 3rd return tank E3 after the 3rd water cooler D3 is cooling, a part flows into the tower top of lightness-removing column C1 as refluxing, a part enters mixing tank A1 and recycles, and taking off the n-proplbenzene that contains of urging the outflow of agent tower C1 tower reactor, the logistics 9 of isopropyl benzene, part 9 is after tower reactor the 3rd reboiler F3 boils again, return to take off and urge agent tower C1, part is drawn.
From the logistics 6 that contains sym-trimethylbenzene, o-methylethylbenzene, unsym-trimethyl benzene and hemimellitene heavy constituent that weight-removing column B1 tower reactor flows out, part 6 is returned to weight-removing column B1 after tower reactor the first reboiler F1 boils again, and part is drawn.
From the logistics that contains m-methyl ethylbenzene, p-methyl-ethylbenzene (m-methyl ethylbenzene, p-methyl-ethylbenzene mix product) 8 that lightness-removing column B2 tower reactor flows out, part 8 is returned to lightness-removing column B2 after tower reactor the second reboiler F2 boils again, and part is drawn as product.
Embodiment 1～6
Carbon nine C9 aromatic hydrocarbons mixtures used are reformation C9 aromatic cuts in an embodiment of the present invention, wherein approximately contain 22.93% (weight) between, p-methyl-ethylbenzene, its concrete component and content see Table 1.
Composition and the boiling point of table 1 C9 aromatic raw material
| The component title | Content (% by weight) | Boiling point (℃) |
| P-Xylol | 0.30 | 138.4 |
| Isopropyl benzene | 0.46 | 152.2 |
| N-proplbenzene | 4.54 | 159.20 |
| M-methyl ethylbenzene | 16.80 | 161.33 |
| P-methyl-ethylbenzene | 6.13 | 162.01 |
| Sym-trimethylbenzene | 6.81 | 164.74 |
| O-methylethylbenzene | 7.61 | 165.18 |
| Unsym-trimethyl benzene | 45.20 | 169.38 |
| Hemimellitene | 12.15 | 176.08 |
By above-described from C9 aromatic the method for compartment, p-methyl-ethylbenzene implement, concrete processing condition, parameter and urgency agent used see Table 2～table 4.
The C9 aromatic raw material be isolated between, the yield of p-methyl-ethylbenzene calculates by following formula:
The separating technology condition of embodiment 1-6 and separating resulting are listed in respectively table 2-4
The separating resulting of table 4 embodiment 1-6
As can be seen from the above results: different according to selected urgency agent kind, inlet amount is different, and reflux ratio is different, adopt method of the present invention all can obtain purity＞98% between, the p-methyl-ethylbenzene product, its yield＞90%, visible separating effect of the present invention is remarkable.
Comparative Examples
At first, 1000Kg C9 aromatic raw material (component and content thereof see Table 1) is introduced from the middle part of weight-removing column, draw the light constituent that mainly contains n-proplbenzene, m-methyl ethylbenzene and p-methyl-ethylbenzene from tower top, draw the heavy constituent that mainly contains sym-trimethylbenzene, o-methylethylbenzene, unsym-trimethyl benzene and hemimellitene from tower reactor;
Then, the light constituent that will be drawn by the weight-removing column tower top is introduced lightness-removing column from the middle part of lightness-removing column, between drawing from the lightness-removing column tower reactor, the p-methyl-ethylbenzene mix product.
Table 5 has provided the concrete operations parameter of weight-removing column and lightness-removing column, table 6 provided obtain between, the composition (% by weight) of p-methyl-ethylbenzene mix product.
Use the method, by separate in C9 aromatic obtain between, the yield of p-methyl-ethylbenzene mix product is 53.5%,, the weight content of p-methyl-ethylbenzene is 94.5%.
The operating parameters of table 5 Comparative Examples weight-removing column and lightness-removing column
| Project | Weight-removing column | Lightness-removing column |
| Stage number/piece | 80 | 140 |
| Tower top temperature ℃ | 160 | 158 |
| Tower reactor temperature ℃ | 179 | 172 |
| Tower top pressure/MPa | 0.1 | 0.1 |
| Tower reactor pressure/MPa | 0.13 | 0.13 |
| Reflux ratio | 35 | 50 |
The composition (% by weight) of table 6 Comparative Examples weight-removing column and the logistics of lightness-removing column tower top tower reactor
The comparison of table 7 Comparative Examples and embodiment 4 compartments, p-methyl-ethylbenzene mixture
From the data of table 7 more as can be known, the weight-removing column reflux ratio is 35 in rectification method, when the C9 aromatic raw material of the 1 ton/h that processes at full capacity when this weight-removing column is, this moment, the vapour phase flux peak of rectifying tower was 36 * 0.2 tons/h, and in same tower, adopt benzene with catalytic rectifying method can be treated to the C9 aromatic raw material of 36 * 0.2/9 * 0.3244/h=2.47 ton/h; The lightness-removing column reflux ratio is 50 in rectification method, when the C9 aromatic raw material of the 1 ton/h that processes at full capacity when this lightness-removing column is, this moment, the vapour phase flux peak of rectifying tower was 51 * 0.07 tons/h, and in same tower, adopt benzene with catalytic rectifying method can process the C9 aromatic raw material of 51 * 0.07/11 * 0.1091/h=2.97 ton/h.Therefore, adopt method of the present invention, feed throughput and obtain between, p-methyl-ethylbenzene mixture purity, yield is significantly improved, and can reach high-quality, the purpose of high yield.
Claims (8)
1. the method for a compartment from C9 aromatic, p-methyl-ethylbenzene mixture is characterized in that:
Comprise following steps:
(1) C9 aromatic mixture and urgency agent are sent into weight-removing column after mixing, drawn the light constituent that comprises n-proplbenzene, isopropyl benzene, m-methyl ethylbenzene, p-methyl-ethylbenzene and urgency agent by the weight-removing column tower top, drawn the heavy constituent that contains sym-trimethylbenzene, o-methylethylbenzene, unsym-trimethyl benzene and hemimellitene by the weight-removing column tower reactor;
The weight ratio of described C9 aromatic mixture and urgency agent is: 1:0.05～0.5;
(2) light constituent described in step (1) is sent into lightness-removing column, drawn the logistics that includes n-proplbenzene, isopropyl benzene and urgency agent by the lightness-removing column tower top, draw m-methyl ethylbenzene, p-methyl-ethylbenzene mix product by the lightness-removing column tower reactor;
The logistics of (3) lightness-removing column tower top described in step (2) being drawn is sent into to take off and is urged the agent tower, urges the agent tower top to draw the urgency agent by taking off, and urges agent tower tower reactor to draw the logistics that includes n-proplbenzene, isopropyl benzene by taking off;
Described urgency agent is acetonitrile and propionitrile;
Described weight-removing column stage number is 30～90, and the weight-removing column tower top temperature is 80～180 ℃, and the weight-removing column tower top pressure is 0.1～0.5MPa, and weight-removing column tower reactor temperature is 170～210 ℃, and weight-removing column tower reactor pressure is 0.12～0.8MPa, and reflux ratio is 2～20.
As claimed in claim 1 from C9 aromatic the method for compartment, p-methyl-ethylbenzene mixture, it is characterized in that:
Described urgency agent is propionitrile.
As claimed in claim 1 from C9 aromatic the method for compartment, p-methyl-ethylbenzene mixture, it is characterized in that:
The weight ratio of described C9 aromatic mixture and urgency agent is: 1:0.05～0.3.
As claimed in claim 3 from C9 aromatic the method for compartment, p-methyl-ethylbenzene mixture, it is characterized in that:
The weight ratio of described C9 aromatic mixture and urgency agent is: 1:0.05～0.1.
As described in one of claim 1～4 from C9 aromatic the method for compartment, p-methyl-ethylbenzene mixture, it is characterized in that:
Described lightness-removing column stage number is 30～200, and the lightness-removing column tower top temperature is 80～170 ℃, and the lightness-removing column tower top pressure is 0.1～0.5MPa, and lightness-removing column tower reactor temperature is 170～210 ℃, and lightness-removing column tower reactor pressure is 0.12～0.8MPa, and reflux ratio is 5～20;
Describedly take off that to urge agent tower stage number be 5～20, taking off urgency agent column overhead temperature is 80～140 ℃, and taking off urgency agent column overhead pressure is 0.1～0.5MPa, and taking off urgency agent tower tower reactor temperature is 150～190 ℃, taking off urgency agent tower tower reactor pressure is 0.11～0.8MPa, and reflux ratio is 2～15.
As claimed in claim 5 from C9 aromatic the method for compartment, p-methyl-ethylbenzene mixture, it is characterized in that:
Described weight-removing column stage number is 40～60, and the weight-removing column tower top temperature is 90～160 ℃, and the weight-removing column tower top pressure is 0.1～0.3MPa, and weight-removing column tower reactor temperature is 175～190 ℃, and weight-removing column tower reactor pressure is 0.12～0.4MPa, and reflux ratio is 7～12;
Described lightness-removing column stage number is 50～70, and the lightness-removing column tower top temperature is 90～160 ℃, and the lightness-removing column tower top pressure is 0.1～0.3MPa, and lightness-removing column tower reactor temperature is 175～190 ℃, and lightness-removing column tower reactor pressure is 0.12～0.4MPa, and reflux ratio is 7～14;
Describedly take off that to urge agent tower stage number be 8～15, taking off urgency agent column overhead temperature is 80～120 ℃, and taking off urgency agent column overhead pressure is 0.1～0.3MPa, and taking off urgency agent tower tower reactor temperature is 155～175 ℃, taking off urgency agent tower tower reactor pressure is 0.11～0.4MPa, and reflux ratio is 2～5.
As claimed in claim 5 from C9 aromatic the method for compartment, p-methyl-ethylbenzene mixture, it is characterized in that:
Described C9 aromatic mixture from the platinum reforming tower at the bottom of oil, the xylene isomerization byproduct.
As claimed in claim 7 from C9 aromatic the method for compartment, p-methyl-ethylbenzene mixture, it is characterized in that:
In the middle of described C9 aromatic mixture, the content of p-methyl-ethylbenzene is 5～40 % by weight.
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| CN105503500B (en) * | 2014-09-25 | 2017-07-14 | 中国石油化工股份有限公司 | C9Between aromatic hydrocarbons extraction rectifying, the combination extractant and separation method of p-methyl-ethylbenzene |
| CN105503507B (en) * | 2014-09-25 | 2017-07-14 | 中国石油化工股份有限公司 | The method of aromatic hydrocarbons mixture compartment, p-methyl-ethylbenzene |
| CN114516778B (en) * | 2022-01-20 | 2023-09-22 | 浙江大学杭州国际科创中心 | Method for purifying m-methyl ethylbenzene |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0181144A2 (en) * | 1984-10-29 | 1986-05-14 | Exxon Research And Engineering Company | Process for the separation of C9aromatic isomers |
| US4996388A (en) * | 1990-07-26 | 1991-02-26 | The Dow Chemical Company | Separation of ethyltoluene isomers |
| CN101723790A (en) * | 2008-10-30 | 2010-06-09 | 中国石油化工股份有限公司 | Method for separating mixture of m-ethyltoluene and o-ethyltoluene from C9 aromatics |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0181144A2 (en) * | 1984-10-29 | 1986-05-14 | Exxon Research And Engineering Company | Process for the separation of C9aromatic isomers |
| US4996388A (en) * | 1990-07-26 | 1991-02-26 | The Dow Chemical Company | Separation of ethyltoluene isomers |
| CN101723790A (en) * | 2008-10-30 | 2010-06-09 | 中国石油化工股份有限公司 | Method for separating mixture of m-ethyltoluene and o-ethyltoluene from C9 aromatics |
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